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All Journal Chimica et Natura Acta Indonesian Journal of Chemistry Molekul: Jurnal Ilmiah Kimia
Naini, Al Arofatus
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Agriculture, Biological Sciences & Forestry Biochemistry, Genetics & Molecular Biology Chemical Engineering, Chemistry & Bioengineering Chemistry Environmental Science Materials Science & Nanotechnology

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The Sesquiterpenoids from Aglaia cucullata Peel Fruit and Their Cytotoxic Activities Against B16-F10 and HeLa Cancer Cell Lines Supratman, Unang; Anjari, Intan Hawina; Harneti, Desi; Naini, Al Arofatus; Farabi, Kindi; Anwar, Risyandi
Molekul Vol 18 No 3 (2023)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2023.18.3.7900

Abstract

Sesquiterpenoids are terpenoid derivative compounds that have a diverse chemical structure and pharmacological effects. Sesquiterpenoids can be found in many plants of Aglaia which is the large source of natural compounds in the Meliaceae family. This research was aimed to elucidate the structure of sesquiterpenoids from the peel fruit of Aglaia cucullata and their cytotoxic activities against two human cancer cell lines. The n-hexane extract was separated and further purified by various chromatographic methods to yiled three sesquiterpenoids. The structure of these sesquiterpenoids were identified by spectroscopy analysis including MS, IR, 1H-NMR, 13C-NMR and DEPT as well as compared with spectral data which reported previously. The sesquiterpenoid compounds 1-3 were identified as spathulenol (1), alismol (2), and 10-oxo-isodauc-3-en-15-al (3). The cytotoxic activity of three sesquiterpenoid compounds were tested against HeLa cervical cancer cell and B16-F10 skin cancer cell using the PrestoBlue method. Compound 2 exhibited the highest activity against both HeLa and B16-F10 cancer cell lines with IC50 48.11 μg/mL and 57.05 μg/mL, respectively.
The Sesquiterpenoids from the Stem Bark of Dysoxylum excelsum and Their Cytotoxic Activities against HeLa Cancer Cell Lines Supratman, Unang; Kautsari, Arsi; Naini, Al Arofatus; Riyadi, Sandra Amalia; Mayanti, Tri; Harizon, Harizon; Fajriah, Sofa
Molekul Vol 19 No 1 (2024)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2024.19.1.9406

Abstract

Sesquiterpenoids belong to a group of terpenoid compounds with interesting structures that are abundant in natural products especially in higher plants. Sesquiterpenoids have a wide variety of bioactivities with great potential cytotoxic activity. The species Dysoxylum excelsum belongs to the Meliaceae family known as higher plant, but only a few sesquiterpenoids have been reported particularly for their cytotoxic activity. Therefore, this research aims to isolate and elucidate the sesquiterpenoids structure from D. excelsum stem bark and examines their cytotoxicity against HeLa cervical cancer cells. Through various column chromatography separations, four known sesquiterpenes namely β-caryophyllene oxide (1), caryophyllenol II (2), humulene dioxide A (3), and guai-6-en-10β-ol (4) were acquired from the n-hexane extract. Compounds 1-4 were isolated for the first time from D. excelsum species. The sesquiterpenoid structures were elucidated according to Nuclear Magnetic Resonance, Infrared, and HR-TOF-MS analysis. The cytotoxicity compounds 1-4 was determined against HeLa cervical cancer cells by examination with the PrestoBlue method and compound 3 exhibited the most potent cytotoxicity with an IC50 value of 160.74 µM. Keywords: cytotoxic activity, Dysoxylum excelsum, HeLa, Meliaceae, sesquiterpenoid.
Sesquiterpenoids from The Stem Bark of Aglaia cucullata (Meliaceae) and Their Cytotoxic Activity Against A549 Lung Cancer Cell Lines Mustaqim, Iqbal Wahyu; Harneti, Desi; Naini, Al Arofatus; Hilmayanti, Erina; Darwati, Darwati; Nurlelasari, Nurlelasari; Mayanti, Tri; Maharani, Rani; Farabi, Kindi; Hidayat, Ace Tatang; Supratman, Unang; Fajriah, Sofa; Azmi, Mohamad Nurul; Shiono, Yoshihito
Molekul Vol 19 No 2 (2024)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2024.19.2.9823

Abstract

ABSTRACT. Sesquiterpenoids are a class of terpenoid compounds with a remarkable diversity of structures and biological activities. Sesquiterpenoids are primarily found in higher plants, such as the Meliaceae family's Aglaia genus. Aglaia cucullata is a species of Aglaia that is still rarely explored and can potentially contain sesquiterpenoid compounds with cytotoxic activity. Hence, the research intended to isolate sesquiterpenoids from the n-hexane extract of A. cucullata stem bark and evaluate their cytotoxic effect against A549 lung cancer cells. Compounds 1 and 2 were isolated and purified from n-hexane extracts utilizing various chromatographic techniques. The structure of compounds 1 and 2 was determined by analyzing various spectroscopic methods (IR, MS, and NMR) and comparing them to previously reported spectral data. Compound 1 was identified as an isodaucane-type sesquiterpenoid, 10-hydroxy-6,10-epoxy-7(14)-isodaucane, and was first reported in Meliaceae family. Compound 2 was confirmed as an eudesmane-type sesquiterpenoid, eudesm-4(15)-ene-1β,6α-dihydroxy, and was first reported in Aglaia cucullata. Cytotoxic activity of 1 and 2 were investigated in vitro against A549 lung cancer cells using the PrestoBlue assay and resulted in inactive and low cytotoxicity with IC50 values of 292.77 and 90.55 μM, respectively. Key words: Aglaia cucullata, , A549 cell lines, cytotoxic activity, Meliaceae, sesquiterpenoids.
Four Azadirone-Type Limonoids from Chisocheton Pentandrus Stem Bark and Their Cytotoxic Acitivity Against Mcf-7 Breast Cancer Cell Lines Supratman, Unang; Runadi, Dudi; Naini, Al Arofatus; Purnama, Purnama; Mayanti, Tri; Harneti, Desi; Nurlelasari, Nurlelasari; Maharani, Rani; Farabi, Kindi; Nafiah, Mohamad Azlan
Molekul Vol 19 No 2 (2024)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2024.19.2.11085

Abstract

ABSTRACT. Limonoid group belongs to triterpenoid that has undergone further oxidation accompanied by the loss of four carbon atoms to form a furan ring in the chain. This limonoid compound is often found in the Chisocheton genus. Limonoid compounds have been known as compounds with high structural variations and this makes limonoids have diverse and interesting activities, including cytotoxic and anticancer. In the course of our continuing study for limonoid constituents that have cytotoxic activity against cancer cell lines, methanol extract of stem bark from the Chisocheton pentandrus plant provides significant activity. The methanol extract was separated using various chromatographic techniques in the normal and reverse stationary phase to produce four azadirone-type limonoid compounds (1-4). The elucidation structure of 1-4 was determined using spectroscopic methods including, UV-Visible, IR, and 1D-NMR as well as optical rotation. All four known compounds were established as trichilenone acetate (1), toonaciliaton C (2), 11α-acetoxiazadiron (3), and 16β-hydroxydisobinine (4). The cytotoxicity of compounds 1-4 was assessed by examination using the resazurin method, which showed that compound 4 was the promising constituent against the MCF-7 cells with an IC50 value of 43.1 µM and was stronger than its positive control. Keywords: Azadirone-type limonoid, Chisocheton pentandrus, cytotoxic activity, Meliaceae.
The Cytotoxic Evaluation of Steroids Isolated from Dysoxylum alliaceum (Blume) Blume ex A.Juss. Riyadi, Sandra Amalia; Naini, Al Arofatus; Mayanti, Tri; Lesmana, Ronny; Azmi, Mohamad Nurul; Supratman, Unang
Molekul Vol 19 No 3 (2024)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2024.19.3.11439

Abstract

Dysoxylum alliaceum belongs to the Dysoxylum genus (Meliaceae) and there are few reports concerning the phytochemical components of this plant. To examine the chemical constituents of Dysoxylum alliaceum stem bark, a phytochemical study has been conducted and identified five known steroids, 3β,16β-dihydroxy-24(S)-methyl cholestenol (1), ergosta-5,22-dien-3β-ol (2), ergosta-7,24(28)-dien-3β-ol (3), 22(E)-ergosta-6,22-dien-3β,5α,8α-triol (4), and 20α-dihydroprogesterone (5) from its ethanolic extract. Spectroscopic data such as FT-IR, HR-ESI-MS, 1D, and 2D NMR as well as comparison with previously published spectral data were used to identify the chemical structures of compounds 1–5. Furthermore, these steroids 1-5 were assessed in vitro regarding their cytotoxic effect against A549 lung cancer cell lines and revealed weak to inactive with IC50 values ranging from 68.52 to >150 µM. Keywords: A549 cell lines, cytotoxic evaluation, Dysoxylum alliaceum (blume) blume ex a.juss, meliaceae, steroid
24-Methylenecycloartanol Isolated from The Fruit Peel of Matoa (Pometia pinnata) and Its Activity as an Antibacterial against Staphylococcus aureus and Escherichia coli Anwar, Risyandi; Arnov, Steffi Triany; Putri, Ghesta Alifka; Sinaga, Siska Elisahbet; Naini, Al Arofatus; Supratman, Unang
Chimica et Natura Acta Vol 12, No 3 (2024)
Publisher : Departemen Kimia

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.24198/cna.v12.n3.55682

Abstract

Triterpenoids are compounds with highly diverse chemical structures and exhibit interesting biological activities such as antiviral, antibacterial, anti-inflammatory, and anticancer properties. The matoa plant (Pometia pinnata), belonging to the genus Pometia from the family Sapindaceae, has been used in traditional medicine and shows potential as an antibacterial agent. The purpose of this research was to isolate and determine the chemical structure of triterpenoids from the peel of the matoa fruit (P. pinnata) and to evaluate their antibacterial activity against Staphylococcus aureus and Escherichia coli. The ethyl acetate extract from the peel of P. pinnata demonstrated significant antibacterial activity. In this study, a triterpenoid compound was identified, and its chemical structure was determined using spectroscopic methods, including UV, IR, MS, 1H-NMR, 13C-NMR, and 2D-NMR, as well as by comparing data from the literature. The compound was identified as a cycloartane-type triterpenoid known as 24-methylenecycloartanol. The compound was then tested for antibacterial activity against S. aureus and E. coli. The test results showed a minimum inhibitory concentration (MIC) of 500 μg/mL for both bacteria, which was categorized as very weak
Sesquiterpenoids from Dysoxylum amooroides Stem Bark: Isolation, Structure Determination, and Cytotoxicity Against MCF-7 Breast Cancer Cells Gunawan, Latifah; Mustofa, Hidayat Nurul; Naini, Al Arofatus; Harneti, Desi; Hidayat, Ace Tatang; Nurlelasari, Nurlelasari; Maharani, Rani; Mayanti, Tri; Fajriah, Sofa; Awang, Khalijah; Azmi, Mohamad Nurul; Supratman, Unang
Indonesian Journal of Chemistry Vol 25, No 1 (2025)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/ijc.99121

Abstract

Three sesquiterpenoids, guaianediol (1), alismol (2), and spathulenol (3), were isolated from the n-hexane and ethyl acetate extracts of the stem bark of Dysoxylum amooroides. The three compounds were found in D. amooroides species for the first time. The structures of the isolated compounds were identified and established based on an extensive spectroscopic analysis involving HR-TOF-ESI-MS, IR, and NMR data, as well as a comparison with the previously reported works of literature. Compounds 1-3 were further assessed for cytotoxic effects against MCF-7 breast cancer cells. Guaianediol (1) showed inactive activity with IC50 > 100 µM, alismol (2) showed weak activity with IC50 value of 82.1 µM and spathulenol (3) showed considerable activity with an IC50 value of 15.2 µM. A brief structure-activity relationship and comparison with the previous works were also discussed to understand better the role of guaiane- and aromadendrane-type sesquiterpenoids in the biological activity perspective.
Tirucallane-Type Triterpenoids from the Dysoxylum gaudichaudianum Stem Bark: Phytochemical Study and Cytotoxicity Evaluation Against Human HeLa Cervical Cancer Cells Maira, Faizah; Naini, Al Arofatus; Mayanti, Tri; Fajriah, Sofa; Kusumiyati, Kusumiyati; Supratman, Unang
Indonesian Journal of Chemistry Vol 25, No 4 (2025)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/ijc.103523

Abstract

A total of three tirucallane-type triterpenoids were successfully isolated from the n-hexane extract of the stem bark of Dysoxylum gaudichaudianum: 4,4,14-trimethyl-3-oxo-24-nor-5α,13α,14β,17α,20S-chol-7-en-23-oic (1), toonapubesin B (2), and 3β,22S-dihydroxy-tirucalla-7,24-dien-23-one (3). These compounds were isolated from D. gaudichaudianum for the first time. Structural characterization of the isolated compounds was accomplished through a series of spectroscopic analyses, including HR-TOF-MS, IR, and NMR. Based on previous reports, compound 1 was isolated from a member of the Meliaceae family for the first time. The cytotoxic properties of the isolated tirucallane-type triterpenoids were evaluated against cervical HeLa cancer cells. Among them, compounds 1 and 3 were inactive, with IC50 values > 100 µM, while compound 2 exhibited the highest cytotoxicity, with an IC50 value of 29.23 µM, with moderate activity. A structure–activity relationship also indicated the variation in cytotoxicity attributed to substituent effects within the molecular structures. The modification of the side chain in tirucallane-type triterpenoids was shown to be essential for their cytotoxic activity against human cervical cancer lines.
Chemical Constituents from Indonesian Dysoxylum parasiticum (Osbeck). Kosterm and Their Cytotoxicity Against MCF-7 Breast Cancer Cells Harizon, Harizon; Romundza, Febbry; Miharti, Isra; Naini, Al Arofatus; Fajriah, Sofa; Mayanti, Tri; Supratman, Unang
Molekul Vol 20 No 2 (2025)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2025.20.2.16066

Abstract

ABSTRACT. The exploration of naturally occurring secondary metabolites from plants, which serve as direct sources or precursors for new drug development, motivates us to conduct a comprehensive investigation into their presence. Indonesia stands out as a global biodiversity hotspot, boasting a significant number of endemic species that offer a rich reservoir of untapped resources for pharmaceutical, agricultural, and environmental uses. The Dysoxylum genus, belonging to the Meliaceae family, is recognized as a vital source of secondary metabolites and is well-known for its traditional medicinal applications. Consequently, we focus on analyzing the chemical constituents found in the stem bark of one Indonesian Dysoxylum species, specifically D. parasiticum (Osbeck) Kosterm., and assess their biological activity as anticytotoxic agents. Our research identified three known compounds: a tirucallane-type triterpenoid, cneorin-NP36 (1), a seco-limonoid from the preurianin group, amotsangin A (2), and an ergostane-type steroid, 22(E)-ergosta-6,22-dien-3β,5α,8α-triol (3). The biological evaluation against the human breast cancer cell line MCF-7 revealed that compound 2 exhibited a notable inhibitory effect, with an IC50 value of 34.5 μM. The existence of a highly oxidized structure in compound 2, due to its ester substituents, highlights its effectiveness in inhibiting cancer cell proliferation, outperforming the reference drug cisplatin, which has an IC50 of 53.0 μM. These findings indicate that amotsangin A (2) is a promising anticancer agent, particularly in the treatment of breast cancer. Further studies, including in silico analysis and structural modification, are needed to enhance its cytotoxic activity and selectivity. Keywords: Cytotoxic activity, Dysoxylum parasiticum, MCF-7, seco-limonoid amotsangin A, Secondary metabolites
Steroids Produced by Endophytic Fungi (Fusarium phaseoli) Isolated from Chisocheton macrophyllus and their Antibacterial Activity against Escherichia coli and Staphylococcus aureuss Katja, Dewa Gede; Sari, Aprilia Permata; Sinaga, Siska Elisahbet; Nurlelasari, Nurlelasari; Farabi, Kindi; Sofian, Ferry Ferdiansyah; Fajriah, Sofa; Naini, Al Arofatus; Supratman, Unang
Molekul Vol 20 No 1 (2025)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2025.20.1.12727

Abstract

ABSTRACT. Steroids are secondary metabolic derivatives of terpenes containing the tetracyclic ring system known to exhibit fascinating pharmacological activity. Steroids are distributed in various genera of endophytic fungi including Fusarium genus which lives inside a higher tree such as Chisocheton macrophyllus. The purpose of this research is to identify and characterize the chemical structure of steroids generated by F. phaseoli, an endophytic fungus obtained from C. macrophyllus roots, as well as to assess their antibacterial activity against Escherichia coli and Staphylococcus aureus. The brown rice medium was fermented with F. phaseoli for six weeks before extraction with ethyl acetate. The extracts yielded four compounds, identified using spectroscopic methods such as FTIR, HRTOF-MS, 1D, and 2D NMR, and then compared to previously described compounds. Compounds 1-4 were identified as ergosterol (1), ergosterol peroxide (2), atroside (3), and cerevisterol (4). The four isolated compounds were evaluated for antibacterial activity against Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 11229 and displayed activity with MIC50 values of 500 µg/mL. Keywords: Antibacterial activity; Chisocheton macrophyllus; Fusarium phaseoli; steroids.
Co-Authors Ace Tatang Hidayat Anjari, Intan Hawina Arnov, Steffi Triany Azmi, Mohamad Nurul Darwati Darwati Desi Harneti Putri Huspa Dewa Gede Katja DUDI RUNADI Farabi, Kindi Ferry Ferdiansyah Sofian, Ferry Ferdiansyah Gunawan, Latifah Harizon Harizon Hilmayanti, Erina Isramiharti Isramiharti Kautsari, Arsi Khalijah Awang Kusumiyati Maira, Faizah Mustaqim, Iqbal Wahyu Mustofa, Hidayat Nurul Nafiah, Mohamad Azlan Nurlelasari Nurlelasari Purnama Purnama Putri, Ghesta Alifka Rani Maharani Risyandi Anwar Romundza, Febbry Ronny Lesmana Sandra Amalia Riyadi Sari, Aprilia Permata Shiono, Yoshihito Sinaga, Siska Elisahbet Sofa Fajriah Tri Mayanti Unang Supratman